Welcome to Kent Island, the largest island in the Chesapeake Bay, the Gateway to Maryland’s Eastern Shore, aka the Land of Pleasant Living, and our country’s third oldest permanent English settlement, predated only by Jamestown, Virginia and Plymouth, Massachusetts.

Kent Island’s founder, William Claiborne was born in England around 1600. The son of a merchant, Claiborne was, as a young man, intrigued by Captain John Smith’s explorations in the New World’s Chesapeake region. When he was twenty years old, fashionable, handsome, and good with a sword if somewhat short in stature,  Claiborne sailed to Jamestown to work as a surveyor. With his loyalty to the establishment, proven mettle, and skillful performance of his duties, Claiborne quickly rose through the ranks of Jamestown’s leadership. In 1626 he served as the colony’s Secretary of State and in 1627 was granted a license to trade with the native tribes of the upper Chesapeake.

William Claiborne 2

George Calvert was a privileged gentleman, a…

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